Our Trans Canada Trail walk began near Douglas Coupland’s pixelated Digital Orca sculpture in Coal Harbour. I’ve always found it mesmerizing and I wanted to linger for a few minutes, but I felt the clock ticking. We were going to put in over 30 kilometres that day, and we were behind schedule.

It was a perfect morning: chilly but cloudless, the sun already well launched into pale blue sky. The kind of Vancouver day that announces the possibility of a life beyond rain. A nice long walk. Get off-screen and out from under the domestic roof. The sky as my ceiling! Fresh air and fitness! Profundity at every turn!

This was the idea: a two-day urban hike on the Trans Canada Trail. Begun as a national project in 1992, the TCT was renamed the Great Trail in 2016. This was part of a federal rebrand that also bills it as the longest trail in the world at 24,000 kilometres, running from Vancouver Island to the Northwest Territories to Newfoundland. However, unlike other long-distance routes that are actually trails in the way we understand the word—the Pacific Crest Trail, for instance, which runs the backcountry from Washington’s Cascade Range to Baja California—this trail is a patchwork stitching of roads, canoe routes, and biking and hiking paths. The route is more of a bureaucratic fantasy than a reality, and in some spots it’s nothing more than tagged highways no safer, nor any more scenic, than any other road.

But I was curious what the trail’s route would show me of the city. One day with my friend Mark—a boat captain and engineer who works on heritage sternwheelers—and one day solo. The perfect balance of solitude and community. By the second afternoon I would be in Port Moody, celebrating my 2,000-plus calories burned with something indulgent. Lobster bisque. A banana split. Steak. Something.

The photos Mark took that Tuesday morning show me geared up with a backpack and sensible attire: lightweight nylon T-shirt, abundantly pocketed cargo shorts and a full-brimmed canvas hat borrowed (reluctantly) from a retired neighbour. There is something briskly humiliating in wearing a Tilley hat in downtown Vancouver. You are instantly an assumed part of the cruise-ship crowd. This belittlement, actual or imagined, is given an added twinge when—assuming you’re in your mid-40s or above—you realize you are now closer to retirement age, and cruise-shipdom, than you are to your university years.

What Mark’s photos do not show is that I was wearing overused five-year-old running shoes. Despite good intentions, and despite the fact that one’s feet are the crucial equipment on a long walk, they were not bulked up with the prescription orthotics I’d been promising to get for years, either. One rather obvious bit of advice to the would-be urban walker: purchase exceptional footwear.

Our easterly route on the trail began by heading west and using Vancouver’s most famed chunk of walkability—the seawall—to circumnavigate Stanley Park. As we walked down to the seawall path, I checked the time: 9:45 a.m. Still in good shape. I was sure we could bag our distance in seven hours. If you do some light research on average walking speed, the figure that tends to come up is five kilometres an hour. If that was what ordinary mortals could do, surely we could do better. Thirty kilometres in a day. Easy! Put in three hours before lunch, then another three or four after that: we’d be at the odd little motel I’d booked on Boundary Road by late afternoon.

I had several motives for the trip. One was the ambient unease that has set in now that we’re all aware of sitting as the new smoking. I sit a lot. Sometimes I stand while working at my computer, but most of my life is shockingly sedentary. Another, less hypochondriacal, motive was my long-held hope that when my son reaches the right age—12? 16?—we would walk together from where I live in New Westminster to the summit of Mount Baker and back. Doing so would be a fairly epic trek of probably 250 to 300 kilometres, with no clear route. I figured a 55-kilometre walk would help me ballpark my odds of being able to do it in the years to come, should it actually be possible.

Another catalyst was Thoreau, always a likely suspect for inspiring walks (and walking narratives, a literary canon of surprising abundance). In his writings on the subject, he advises readers of the benefits of a long daily stroll. “I cannot preserve my health and spirits,” he writes, “unless I spend four hours a day at least—and it is commonly more than that—sauntering through the woods and over the hills and fields, absolutely free from all worldly engagements.”

Easy, of course, for an unemployed, childless bachelor like Thoreau to prescribe a spiritual regimen of four-hour walks. But no doubt he was right: that would be a hell of a nice way to spend your time if you had no job, mortgage or dependents. Still, I felt I had to find room in my calendar to be more Thoreau-esque, for the sake of living to 60 if nothing else.

Most of my early revelations on the walk, thanks to Mark, were historical. Amid the glass towers and white masts of Coal Harbour, for example, I learned about the rum-runners who made boatloads of cash off America’s Prohibition. The trade ran via cargo schooners like the 246-foot Malahat—a ship owned by the Reifel family, who made their fortune in contraband booze and gave our city the Commodore Ballroom, the Vogue Theatre and the Reifel Migratory Bird Sanctuary.

Mark is that rare type of well-read Renaissance man who sheds historical tidbits like these the way a plum tree drops ripe fruit. He also reads (and writes) contemporary poetry and can fix a Cummins diesel. His unique fusion of craftsman, historian and aesthete was summed up by a moment at Granville Island when, after nearly four hours of walking, we were sitting down to lunch. I caught him staring at the ceiling above the Blue Parrot coffee shop.

“What are you looking at up there?” I said. I thought there might be a pigeon about to crap in my butter chicken.

He was rapt; he didn’t look down. “Just admiring the hypnotic symmetry of these old trusses.”

Talking history passes the time, but it doesn’t make you walk faster. It was 1:30 p.m. when we got to Granville Island. It had taken us three hours and 45 minutes to go about 16 kilometres. So much for five kilometres an hour. But we weren’t worried: at this rate, we figured, we’d be at the motel by early evening. We set off, the trail wending us down False Creek and through Chinatown and Strathcona.

By the time we got to Hastings-Sunrise, we’d left history behind us and were walking mostly in the moment. It was an afternoon of strong, leaf-flashing winds and warm sunlight. The wind came rushing at us from over the silhouetted shoulders of the North Shore mountains, whistling through the treed avenues. It was a perfect moment, heightened by endorphin-induced grace notes. When we stopped near the perfectly named Dusty Greenwell Park—perched on the edge of the railroad and overlooking Burrard Inlet and an industrial lot of empty shipping containers—I felt like we were at the centre of the world.

Our earlier time calculations turned out to be optimistic. We didn’t arrive at the motel—a place remarkable for being completely unremarkable, and offering a view of a massive intersection—until close to 9 p.m. This was after a beautiful, windswept rest on driftwood logs at the New Brighton beach and after the very long, torturous and terrible last four kilometres down the radically unscenic Boundary Road.

I had come into the walk with low-grade foot pains—the kind that, as a computer-bound sedentary, you can generally ignore completely. They had begun to flower hours before, somewhere in Strathcona. By the time we got to Boundary I was visibly hobbling and experiencing a novel sensation: burning needles zinging out laterally from my ankle joints. My left knee hurt, and I thought I might have a hairline fracture in the arch of my right foot. My pace was slowed by seeking out forgiving patches of grass on which to tread instead of the punitive, hateful sidewalk. Minus our leisurely 90-minute lunch on Granville Island, we’d been walking for nine and a half hours. There is not much to say about the discomfort of walking on concrete in subpar footwear for that amount of time, except that it sucks and you should avoid it.

At a nearby Chinese restaurant Mark and I gratefully collapsed into chairs and ate a huge dinner, toasting our epic day: 33 kilometres on foot. He caught transit home, and I slept the sleep of the truly exhausted back at the motel.

The next morning I set out boldly, blessed with good weather and feeling no pain. I enjoyed walking the slightly surreal neighbourhood at the top of Boundary, where well-manicured lawns part like the Red Sea to make way for an army of power line towers marching up the hill. There, a few blocks from Mont-rose Park, I stopped for a few minutes—and lo, it was quiet. Chirps of chickadees and blackbirds, and the distant ssshhh of bridge traffic. It was midweek and no one was around; they were all below, working, commuting, computing. I felt a bracing, Words-worthian sense of apartness.

Thoreau wrote, “Two or three hours’ walking will carry me to as strange a country as I expect ever to see. A single farm-house which I had not seen before is sometimes as good as the dominions of the king of Dahomey. There is in fact a sort of harmony discoverable between the capabilities of the landscape within a circle of
10 miles’ radius, or the limits of an afternoon walk, and the three-score-years and 10 of human life. It will never become quite familiar to you.”

This is definitely true. But 150 years after he wrote those sentences, more than 80 percent of Canadians live in cities—and globally, by 2050, we will be over six billion urbanites. These cities are not, for the most part, the woodsy, wetland environs that Thoreau loved. They are landscapes of damage. The vast grids of incursion we call cities include green-space parks and prim neighbourhoods, but also at least as many stinking alleys, traffic-choked arterials and industrial wastelands—populated with abundant evidence of our dependence on chemicals, fossil fuels and plastics.

So the pastoral contentment Thoreau sought in his walks is not quite the same for us urban moderns. But along with a degree of ecological radicalization, there is still that chance, while out on foot, of being charmed by where you live—to have your wait for the angel satisfied by a transcendent glimpse or two. In a world drowning in novelty, most of it digital, there is something to be said for finding the unfamiliar in one’s non-virtual backyard. You talk with the owner of a local store for 10 minutes about music, local architecture, where to buy fresh fish. You spot a faded mural on the backside of an old brick building, or a fresh and arresting work of graffiti. Straying beyond these ruts on an agenda-free walk gives us a chance to hold where we are, and even our own lives, at arm’s length for a little while.

My various foot and joint pains returned with vigour not long after I crested Boundary Road, blunting my enjoyment of Confederation Park and the Burnaby Mountain woods. I got a sweeping view of Indian Arm, then took off my pack and sat on a bench for a traditional European road lunch—crackers, cheese, dry sausage. (Or rather, to be honest about my fussy urbanite tastes: some gluten-free crackers, Mt. Lehman goat beer cheddar, caraway landjäeger sausage from Oyama’s on Granville Island.)

When I stood up from the bench, I saw it was dedicated to one Bernie Savage, who died at age 50 in 1998. Fifty? Yes, my math was right. Poor Bernie. I would be blowing out 50 candles soon enough. Hopefully.

As I made my way to Port Moody, I was struck by the industrial developments along the route—the odorous refinery, a sulphur transfer facility—and intermittently depressed by the ubiquitous plastic garbage cluttering the roadsides. But I became increasingly elated the closer I got to Port Moody. When I finally peeled off my backpack (and my shoes, etiquette be damned) at the Boathouse Restaurant in Rocky Point Park, I celebrated with a solid steak dinner and a dram of whisky.

I did feel victorious, but the dominant feeling was relief. The punishment was over! As a recon walk for a possible longer trek, I’d been forewarned. If I were going to saunter to Mount Baker with my son, I would need the right shoes, likely something expensive and custom. And more regular walking. And some rehab. A couple of weeks after the trip, when I described my panoply of newly discovered foot aches to my newly discovered podiatrist, he looked at me and nodded. “Right,” he said. “Disneyland syndrome.”

This, he explained, was his term for a phenomenon he saw weekly: middle-aged parents who had just spent several eight- to-10-hour days wandering asphalt and concrete in bad shoes. So besides getting the good footwear (this repeat message brought to you by your future metatarsal stress fracture), here is another tip for those considering pilgrim-length walks: whether tramping the Camino de Santiago or the outskirts of Burrard Inlet, allow yourself to saunter.

Limit yourself to under 15 kilometres a day—at least in your first few days, if you’re doing a multi-week trip like the Camino. Walking five kilometres an hour is definitely possible, particularly as your shanks regain some of their vigour. But don’t press yourself into that kind of stride and purposefulness if it runs against the spiritual grain.

Thoreau had it right: four hours is optimum. And walking 15 klicks or less in that amount of time allows for the kind of soulful traverse that, in the end, should be the point. It allows for conversation if you can get it and reflection if you can’t. More distance than that and it starts to feel like a forced march. Wake up, have your breakfast and hit the road. Then have a well-deserved lunch, and spend the rest of the day in repose—reading, writing, cultivating the civic virtues. Allow for the unseen. Take it slow.